TOW It Works
by itsafour
Summary: After a one-night stand, Chandler and Monica realize they want to have sex again at least once before flying back to New York. What if they manage to do it? - Set on season 5, on TO After Ross Says Rachel. Smutty series of standalones.
1. Chapter 1

**_Author's note: Hey there! Here I am with a new multi-chaptered fic haha but not that long this time._**

 ** _So, the idea here is very simple: what if each moment in which they had tried to have sex on TO After Ross Says Rachel had actually worked out?_**

* * *

"So, look, um… while we're still in London, I mean, we can keep doing it, right?" That was a long shot but Monica was willing to try anything. They had just agreed that doing it again would be a risk to their friendship, that they shouldn't have let it happen in the first place – especially not seven times –, but deep down all Monica wanted was to blow off this wedding – that was already ruined by the groom anyway – so that she could get somewhere with Chandler and do it again.

"I don't see that we have a choice!", he emphatically agreed, "But, when we're back home, we don't do it."

"Only here." She confirmed, making sure they were in the same place.

"Y'know, I saw a wine cellar downstairs..."

 _Say no more._ "I'll meet you there in two minutes."

"'K!" The way he threw his plate away – it had food on it! – in order to run to the wine cellar just confirmed that he wanted this as much as she did. Monica started checking herself out, getting ready to have some amazing sex with her friend again when she was intercepted by Rachel.

"Mon, honey, I gotta ask you something."

"Now?" She didn't mean to sound so impatient but her desire had taken control over her body by that point. What Rachel could possibly want from her, for Christ's sake?

Of course it had to do with Ross. Monica wanted to be supportive, she really did, but as she mindlessly spilled some self-help clichés, she took care of her breath and watched the door, calculating the way she would go to follow Chandler. Rachel seemed confused and decided to confront Ross, and, at that moment, the good friend in Monica spoke louder than the desperately horny one, and she had to pull Rachel back and put some reason into her little brain.

"Wait! Rachel, no. He's married. Married! If you don't realize that, I can't help you." She wished that would be enough.

"Okay, you're right. You're right. You can't help me." And Rachel left. Monica sighed in frustration but at least Rachel wasn't holding her back anymore and she could finally get to that damn wine cellar.

As she went downstairs, anxiety took over. Was she really going to a) have sex with her friend b) at a public place c) during her brother's wedding when d) her brother was actually going through what seemed to be the biggest crisis in his life and also e) an unreasonable Rachel was walking around the reception? It wasn't like her to leave her friends to their fate like that, but at that moment she couldn't afford to put them first. Something unbelievable had just happened in her life and she had to enjoy it right now because she knew that, once they were back home, it would be over.

When she got there, she took a deep breath. She could feel she was shaking – was it the excitement from what they were about to do? Was it fear? Was it regret? Maybe she was shaking from all of those things combined – either way, she wouldn't stop there. She pushed the already open door, revealing a startled Chandler who was leaning onto the wall, next to some barrels. He looked dreamy; Monica smiled despite herself while she closed the door.

"Hey," hands in pockets, he moved to her, his eyes scanning her whole body. Monica's shivering intensified at that.

"Hey," she responded, placing her little purse onto a barrel and getting closer to him too.

She felt like she was drowning in all the things she wanted to say. However, if she had the time to talk, Monica had no idea what they would talk about. Her mind was overflowing with ideas and yet she was speechless.

Every second it took for him to touch her made breathing an activity way too hard for Monica. When his fingers softly touched her cheek, she allowed herself to close her eyes and wait for the moment their lips would finally meet again. When they did, it felt amazing. It'd been less than 24 hours since the last time she had tasted his lips, but feeling that softness again only made her realize how much she already craved it. _I'm screwed,_ she concluded, already dreading their return to a routine in which this would need to be avoided and forgotten.

His tongue parted her lips to force an entrance, an act that caused her to moan and wrap her arms around his neck. With their open mouths, the previously soft kiss became heated, energizing their limbs, which started moving around each other's bodies, looking for places to grope and caress. When Chandler pressed against her even harder, Monica could feel how stiff he already was, and she wanted to speed the process so that he could see how aroused she was too – the wetness she could feel between her legs informed her of that.

Not wasting any minute, her hands left their previous spot to unbutton his vest and start getting rid of his so many layers. At that, he broke the kiss to suck on her neck and leave pecks onto her shoulder (mindful of their surroundings, Monica was surprising herself by how little noise she was making – she wouldn't risk the present opportunity by getting caught).

She was almost done with his white shirt, the last goddamn layer covering his soft skin, when his hands wandered around her back, getting down until finding on her buttocks a place to rest. He squeezed them as Monica took off his shirt, and they were back to some passionate kissing. When they broke apart again, flushed and apparently ready to go, as if in tune, they started looking around, seeing if they could find something to lean on or maybe sit onto. They seemed ready to do it up against the wall there should be no other choice, but Monica found a chair. With no warning at all, she started pushing him – he walked backwards, for some reason trusting her judgment even though she hadn't asked him to. When the back of his legs reached the chair, she gave him a little push, making him fall into a sitting position.

With no further ado, she kneeled in front of him, tugging his pants down, not really bothering to take them off completely but making sure they weren't covering his genitalia anymore. For a second, she just stared at his penis, memories from the previous night flashing behind her eyes – she could swear she felt like she was hungry, mouth full of saliva and everything. She only wanted to do one thing, so she went for it, grabbing his member and shoving it into her mouth.

Chandler's head was hanging in pleasure, and when Monica looked up, she could see his strained neck and pale, soft, bare torso, which made her moan around him, which also made him groan in return. She couldn't get enough of his taste – he just tasted so damn good. His texture felt great against her tongue, and he was girthy and lengthy enough to excite her but not really hurt her. She wanted him as deep as possible; she forced him against the back of her throat, getting more and more aroused by the minute at every sound that he made. She had been sucking him off with closed eyes, enjoying his delicious taste with every fiber of her soul, so she was surprised when she felt his hand clutching her hair. When she opened her eyes and looked at him, he was watching her with a face that almost said "I can't believe this is happening", and, truth be told, she couldn't believe it either. Monica had somehow expected things to be a little more difficult, but there she was, giving him a blowjob at someone else's house and soon enough having him inside her.

Monica stopped her activity and stood up again. Chandler pulled her; she stood between his open legs as his hands roamed her still clothed body. He reached the zipper on her back and fumbled with it a little before getting his way around it and pulling it open, revealing her skin – she wasn't wearing a bra and he moaned just by looking at her breasts out in the open. Her nipples were very hard – he just went for them, sucking, licking, and biting them while his hands continued his job of taking her dress off. When he finally did it, he wasted no time pushing her panties down too, leaving her only on heels. His mouth was still playing with her breasts when his hands started two different jobs – one going for her back, alternating between tracing her crack and squeezing her ass and another one going for her front, fingers spreading her labia and penetrating her while his thumb rubbed her clitoris.

She was going crazy – that felt so good, she could probably stay in that position forever, taking advantage of his tongue, his lips and his fingers for all eternity. Actually, no. She couldn't do that forever because more than ever she needed that man inside her. Monica stopped him – he looked like a child having his toy mercilessly taken away from him –, leaning down to kiss him softly before setting herself onto his lap, straddling him. One arm wrapped around his shoulders, the other one going behind her to grab on his penis and position it against her entrance. A swift movement later, he was inside her again, and she felt complete. For a moment, they just stared at each other – the realization of what they were doing suddenly sinking in. They weren't drunk anymore. It wasn't a dream or a fantasy. It was real life. She had Chandler inside her. She had his face inches apart from hers and his body pressed against hers. And, the most surreal part was that somehow it all felt way too good. She could swear he was having similar thoughts as his blue eyes showed her a mix of fear and excitement, probably in equal amounts. She could relate to that, and he probably could see a mirror of his feelings on her expression. They could also make it all less overwhelming and more enjoyable by kissing each other and finally moving – as if they had just realized that together, they did it. Monica's hips easily went up and down as they kissed between moans. There was a steady pace and, as it got faster, their kisses got sloppier and they both seemed to be close to a climax.

She came first, moaning against his neck, and soon after she felt him tense up as he came too. Her arms were wrapped around his shoulders, and her head hid in the crook of his neck. Chandler's arms, on the other hand, wrapped around her middle, flat hands against her back. They remained in that position for a long time, although she couldn't tell how long. Monica was profoundly afraid of letting him go and, as a result, losing… this. Losing whatever she'd managed to acquire in that hotel room the previous night. When he suddenly started kissing her shoulders she honestly felt like crying on the spot.

"Y'know…" He said, and she prepared herself for whatever he was about to say. "Maybe we should consider going on wine tours when we're back in New York."


	2. Chapter 2

Gears were turning in Chandler's brain; he was thinking about all the places they could go to – Monica seemed to be doing just the same – and the easiest solution was obviously the hotel they had slept in the previous night. They had silently agreed on that as they looked at each other on their way out and Chandler felt like some lame teenage boy – seriously, Monica's stare had always been _something_ but it had never made him shiver like that before, especially not to the point of almost getting him hard. He could feel embarrassed by how he was easily aroused by the woman next to him but he felt like this reaction was only natural.

The reason they were headed back to their hotel was the fact that the little visit to the wine cellar had not worked out. Chandler had been on his way to the room when he'd heard people talking about going there soon, and when Ross's new father-in-law had confirmed the information, Chandler had dejectedly come back to the buffet, mindlessly poking some food to release his frustration. It seemed that he hadn't given up yet though – neither had Monica – so realizing that doing it at the Waltham's house would be impossible had only made them think about where else they could go to and the hotel, which was next to the house, was the best option.

They walked there, thanking the gods for their friendship, since it allowed them to go around places together without raising any suspicion. Chandler's mind was full of dreams and memories, and they were all mingling. He just wished he could get to her room soon and do all sorts of things to Monica's body – the same things he'd done the previous night (maybe some new ones). Whatever would happen, he was happy that she was willing to have sex with him one more time – all his energy went to being excited about what they were doing at the moment because he was trying really hard to push away the fact that, eventually, they wouldn't be able to have sex again. _I'll only cross that bridge when I come to it, now we just need a place._

Each step closer to her room had him jumping with joy. "Listen, in the middle of everything, if I scream the word 'yippee', just ignore me." He said in all honesty, making her laugh.

When she finally opened the door, they were met with Rachel, who was sitting on Monica's bed.

"Oh, my God, Rachel! Hi!" Monica's voice came out shaken.

"Oh, hello, Rachel." And his own voice was less enthusiastic than the ordinary tone used for a greeting.

How did she beat them to the room, Chandler wondered, not very interested in getting answers – he'd rather think about ways of getting her out of there.

"Ross said my name, okay? My name. That obviously means that he still loves me!"

They couldn't even properly reply Rachel's statement, much less because she was obviously crazy and much more because their brains were too busy coming up with ways of taking the place back to themselves.

"Y'know what? Don't believe me, I know I'm right. Do you guys want to go downstairs and get a drink?"

"Yes, we do." Chandler didn't waste a second answering that, which alarmed Monica. "But, we have to change first."

And then she got it. "Yes, I want to change." Bless her fast thinking. "Why don't you go down and get us a table?"

"Yeah, we'll be down in like five minutes."

"Fifteen minutes." She corrected him as fast as she elbowed him. He winced a little but no biggie – if she wanted more time, he wouldn't be the one to complain.

"Okay then. See you guys downstairs." Their friend grabbed her purse and left, and when she closed the door behind her, Chandler and Monica let out the air that had been stuck in their lungs during that brief yet painful interaction with Rachel.

"Can you believe that-" Chandler attempted to say something but was interrupted by Monica throwing herself at him to kiss him fiercely. It hauntingly reminded him of the previous night, but this time he didn't take that long to understand what was going on and kiss her back. One hand flew to her hair, untying it and making it fall down – it felt soft on his fingertips – and the other hand squeezed her ass. She moaned into the kiss, then broke it apart to look at him. _My God, this woman is stunning._ Her face was all red, her lipstick a little smeared from the kiss, her hair albeit disheveled was framing her face beautifully and her eyes had that glint, that spark, that _something_ that only Monica had – something that mixed insecurity and mischief in a way that made her so irresistible.

"Five minutes, huh?" She teased him as she kept giving him quick pecks around his lips.

He chuckled against her jawline then pulled back to look at her eyes. "Well, this time being fast is not a personal choice of mine."

"You weren't fast last night…" She gave him a devilish smile, kissing him again and biting his lower lip. "Not at all."

"Sometimes you need to take your time to reeaaally enjoy the moment."

She giggled, walking backwards and pulling him along. They both reached the bed and plopped down onto the mattress. Her hands didn't bother with the clothes on his upper body, going straight to his belt and the zipper on his pants. He let her lead – it was unbelievably hot seeing Monica so eager to have sex with him to the point where she didn't care about getting completely undressed.

He pushed down the straps of her dress to freely kiss her shoulders then started pulling her dress up, bunching it up over her waist, and tugged her panties down. His penis was very hard and his pants were no longer in his way – he could enter her right there if he wanted to (he definitely wanted to) but he actually wanted to work her up even more. With her underwear hanging on one ankle, Monica's legs were wide open, just waiting for him, but all Chandler did was scoot down on the mattress to get his head between her legs. When he got there, he pressed her thigh against the bed with one hand and touched himself with the other one. His nose sniffed her middle area, taking in her wonderful scent, which worked wonders to get him even more aroused, then he darted his tongue out to start licking her.

"Chandler… Ah, we don't have- m-much time…" but Chandler digressed – there was always time for doing _that_. He licked her entrance and worked in circles on her clitoris while she tugged onto his hair with one hand, the other one covering her own mouth to stifle moans. When he felt like she was close enough, he abruptly stopped the activity, scooting over her and entering her with no warning. She could no longer control her noises – to try and do something about that, Chandler's own hand covered her mouth while his other one steadied her hip so that he could pound into her. Her legs wrapped around his waist and he could swear nothing in the world could ever compare to that particular sensation. She had one hand gripping onto his shoulder and another one holding his cheek while they kissed each other. When they broke the kiss apart, she firmly stared at him as he thrust into her and that was it; he came so hard he felt like he was about to pass out, and right after that he felt her inner walls clenching around him (so _so_ tightly he was almost scared of never being able to get out of her again).

They kissed again, basking in the afterglow of their orgasm. He wanted to tell her something but he didn't know what to say. Somehow, he felt like she was struggling with the same problem.

"Chandler-" Her voice was low, and his heart started beating frantically. The anticipation almost made him miss the sound of footsteps and door opening and when Chandler came back to his senses he was completely under the covers. It seemed that Monica's thinking was faster than his. He heard some muffled conversation and could tell that Rachel was giving Monica the third degree.

"Why are you still here? Are you going to bed _now_? Where's Chandler?" He heard the three questions being shot like fire and wanted to help Monica somehow, but he knew that Rachel knowing he was there would only make things worse.

Monica replied with some lame excuses, which included one about "Chandler changing in his room", and let out a fake fake fake yawn, claiming she was actually too tired to get a drink. "I think I'm going to sleep now."

He could hear the disappointment in Rachel's voice but for some reason she accepted that and just left – he concluded she was too invested in her own screwed up love story to really notice what was going on in that room.

As he rose from under the covers, he was met with Monica's lovely face – she was laughing at the absurdity of the situation, which made him laugh too. Then they were both laughing way too hard, lying on their sides, staring at each other.

He felt awkward and scared and comfortable at the same time – he knew that all the conflicting feelings had to do with the fact that he had just had sex with Monica and, this time, it wasn't possible to blame it on the alcohol. Chandler could feel panic looming over but it dissipated as soon as Monica leaned in to softly kiss him. He kissed her back, his hand instinctively going for her hair.

When she smiled at him, his heartbeat was so out of control he didn't know if he was happy or about to have a heart attack.

"I guess we have way more than five minutes now."


End file.
